Potassium Iodide → (4-Fluoro-phenyl)-(5-iodomethyl-pyridin-3-yl)-methanone

HRID 556275Notes

Reaction equation

HRID 556275 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[O:10])[CH:6]=[N:7][CH:8]=1.[I-:18].[K+]>CC(C)=O.C(Cl)Cl>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]([C:5]2[CH:6]=[N:7][CH:8]=[C:3]([CH2:2][I:18])[CH:4]=2)=[O:10])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 4875Potassium IodideHCID 59200177(5-Chloromethyl-pyridin-3-yl)-(4-fluoro-phenyl)-methanone

Product 1

HCID 66671616(4-Fluoro-phenyl)-(5-iodomethyl-pyridin-3-yl)-methanone

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-chloromethyl-pyridin-3-yl)-(4-fluoro-phenyl)-methanone (1J) (220 mg, 0.88 mmol) in 5 mL of acetone at room temperature is added potassium iodide (590 mg, 3.6 mmol). After being stirred at room temperature for 3 hours, the reaction mixture is diluted with 50 mL of CH2Cl2 and washed with 5 mL of water. After concentration, the residue is dissolved in 15 mL of CH2Cl2 and washed with 2 mL of saturated sodium hyposulfite. After being dried, the solution was concentrate to give a 80/20 mixture (by 1H NMR) of (4-fluoro-phenyl)-(5-iodomethyl-pyridin-3-yl)-methanone (1F) and the starting chloride (1J) as light yellow solid that is used without further purification for next step reaction. MS (ESI) m/e 342 (M+H+).

Workup

  1. washwashed with 5 mL of water
  2. concentrationAfter concentration
  3. dissolutionthe residue is dissolved in 15 mL of CH2Cl2
  4. washwashed with 2 mL of saturated sodium hyposulfite
  5. customAfter being dried
  6. concentrationthe solution was concentrate

Sources & evidence

ORD record
ord-e11acdc4fc65421aaa3825a422b5bde8
Source dataset
uspto-grants-2011_11
Patent number
US08058272B2

Reaction notes

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